Cycling Holiday Tuscany
A land of elegance, beauty and dreams
An overview of our cycling holidays in Tuscany
Tuscany a land of beauty, elegance and dreams. Where the colours of the landscape and the flavours of the traditional cuisine change with the seasons, and the slow rhythm of life is felt with each encounter, ride and meal.
To the cyclist who ventures into this world, it is heaven. Urged by a sense of adventure and the discovery of magnificent views at every turn, you can expect long, warm days on our Tuscany cycling tours surrounded by incredible panoramic views of rolling hills, olive groves, vineyards and medieval hilltop towns, all while embracing the winding roads, challenging climbs and exhilarating descents.
Rediscover your taste for adventure on our Tuscany cycling holiday as you pedal along quiet country roads and cobblestoned streets, enjoying the history, culture and of course the cuisine of this spectacular region.
Tuscany is where our journey began and a place we invite you to share with us as we create a truly authentic experience of our favourite areas to ride and eat in this ancient land, where the art of living is represented through tradition, generosity and talent.
Come ride, eat and drink like a Tuscan. You’re in for an unforgettable adventure.
Tuscany Cycling Tour Ride Itinerary
Welcome to our Tuscany Bike Tour
You’ll enjoy daily rides through the superb Tuscan countryside, taking in the densely forested hills of Chianti, the open rolling hills of the Val d’Orcia and the magical countryside of the San Gimignano province. Post ride on our cycling tours of Tuscany, we’ll enjoy free time in the mid to late afternoons, making the most of the stunning places we stay.
Welcome to ChiantiFollowing our welcome lunch, today’s ride to a hilltop hamlet is the perfect introduction to Chianti with the idyllic rolling hills striped with vineyards and backed by dense wooded forests and the little villages that dot the landscape.
Highlight: The picturesque hilltop hamlet
Distance: 35.9km
Elevation: 719m
To Siena & BeyondIt’s time for you to explore on our bicycle tour of Tuscany the sensational cypress lined backroads of Chianti, made famous by its wine, beautiful winding descents and climbs with incredible panoramic views.
Highlight: The winding descent from Radda in Chianti
Distance: 89.6km
Elevation: 1601m
Climbers ParadiseToday you explore the beauty and challenge of the Chianti hills, with the ride including more sustained climbing with 5 distinct climbs as we traverse through some of the most iconic vlilages between Siena and Florence.
Highlight: The free flowing descents that follow the 5 climbs.
Distance: 75km
Elevation: 1733m
South of SienaToday’s ride will take in three distinct climbs as you get to see first hand the truly majestic Val d’Orcia that was included as a UNESCO World Cultural Landscape in 2004, on your way to the mesmerising Montalcino, home of the sensational Brunello d Montalcino.
Highlight: Riding through the ancient hilltop town of Montalcino
Distance: 82.6km
Elevation: 1662m
A Renaissance adventureToday you set off in the direction of Umbria, in true L’Eroica style you take to the ancient Roman roads (affectionately
known as the Strade Bianche) as you traverse through this postcard perfect landscape and pretty villages, before reaching one of Tuscany’s prettiest towns, Montelpuciano.
Highlight: The open rolling hills of the Val d’Orcia
Distance: 67.2km
Elevation: 1354m
Into Brunello CountryYour longest day, setting off in the direction of Umbria and traversing through a picture-postcard landscape through tiny villages, before reaching one of Tuscany’s prettiest towns, Montepulciano.
Highlight: The quiet and open landscape around Montepulciano
Distance: 68.1km
Elevation: 1286m
Our Tuscany bike tour takes you to the town of 14 towersThis is a truly typical Tuscan day on the bike where you will encounter undulating quiet country roads amidst the rolling hills, woods, olive groves and vineyards as you wind your way from the Val d’Orcia to what many consider is the most beautiful part of Tuscany,
Highlight: The final kilometres with vista of San Gimignano and its 16 towers in the distance.
Distance: 105.3km
Elevation: 1631m
Pricing & Dates
7595
per person twin share / Maximum 14 guests
Show Price As
2025
Start Location & Details
City: Florence, Italy
Pick Up Location: Santa Maria Novella Train Station, Florence
Pick Up Time: 11:00am
Finish Location & Details
City: Florence, Italy
Drop Off Location: Santa Maria Novella Train Station, Florence
Drop Off Time: 11:30am
Inclusions & Details
Accommodation & Meals
- Our Tuscany cycling tours include 7 nights accommodation, twin share with private bathroom.
- Single occupancy available. Talk to us when booking
- All breakfasts
- Lunches on the road
- All dinners at a range of our favourite restaurants and osteria’s, including local wines at each dinner*
- *wine provided at dinner is to accompany meals / beverages ordered by guests will incur additional charges
Ride Support
- Professional bilingual ride guides with extensive cycling experience, local knowledge and first aid experience, ensuring your riding experiences are truly local and take in many of the undiscovered back roads and rolling hills of this spectacular and diverse region.
- Unique GPS routes, provided on tour as part of our bike tours in Tuscany.
- Support van on daily rides, with mechanical support and your safety as our priority.
- Nutritious snacks and water are provided
Transfers & Activities
- All transfers / transportation from pick up to drop off, including baggage and bike transportation.
- Entrance fees to sites and tours / activities included in non riding partner program
Ride Kit
- 2 piece, Italian made A’QTO Cycling Kit including jersey and bib shorts.
- Laundry for your cycling clothing.
Not Included
- Airfare.
- Bike hire.
- Travel & International Medical Insurance
- Guide Gratuities
- Specific gels and energy bars
Have More Questions About Our Tuscany Cycling Tour?
Bike Hire & Gear
Carbon Road Bike with Electronic Shifting
You can choose to hire a Wilier Cento 10SL carbon road bike with Sram Rival Etap, a compact crankset, with a 32 rear cassette & disc brakes.
Carbon Road Bike with Mechanical Shifting
You can choose to hire a Bianchi Sprint with mechanical Shimano Ultegra groupset, a compact crankset, with a 32 rear cassette & disc brakes.
Non-Riding Partners
As part of our cycling tour of Tuscany, non-riding partners enjoy an active and dedicated travel program, designed to deliver a diverse range of activities and the best experiences Tuscany has to offer. Whether its guided walks in the hills of Chianti and the Val d’Orcia, visits to beautiful castles and hilltop towns, meet the producer experiences or cooking classes, non-riding partners experience the beauty and uniqueness of each area we visit. With an itinerary curated by Nancy and delivered together with a range of partners and guides whom she personally selects, It’s sure to be a holiday in Tuscany you’ll never forget.
As our non-riding partner program is an active adventure, there is a minimum walking requirement for non-riding guests for each tour. Please enquire when booking
Accommodation
Food & Wine
Enjoy with us the distinctly different areas of Tuscany and their varied recipes and wines.
The lure of the Tuscan table is immense; characterised by its close association with the land, Tuscan cuisine is earthy, simple in style, and reflective of the region’s changing seasons. We will take you on a food safari of Tuscany that takes in all the very best it has to offer from simple organic produce, grown on our host properties, to exquisite gastronomic dishes at a selection of family-run osterias and restaurants.
Testimonials
THOUGHTFULLY PLANNED & SEAMLESSLY EXECUTED
The ride routes took us through iconic Tuscan landscapes, towns and villages, and when you thought the scenery cold not get better, around the next corner it did. The free-flowing, sweeping descents were an exhilarating reward for the climbing beforehand. The atmosphere throughout the tour was warm, friendly and inclusive and there was a good balance between riding/activities and free time. The accommodation was exceptional, with locations appropriately chosen to make the most of the beautiful Tuscan landscapes and the hosts were warm and friendly, making you feel as though you were part of their family.
